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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
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A Solid Iridium Catalyst for Diastereoselective Hydrogenation.

Iuliia Romanenko¹, Louis Jaffeux², Laurent Veyre¹

¹Université de Lyon, Institut de Chimie de Lyon, Laboratoire de Chimie, Catalyse, Polymères et Procédés, UMR 5265 CNRS-Université Lyon 1-CPE Lyon), Équipe Chimie Organométallique de Surface, 43 Bd du 11 Novembre 1918, 69616, Villeurbanne, France.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|September 24, 2017

Summary

A novel supported iridium catalyst significantly enhances the diastereoselective hydrogenation of terpinen-4-ol to cis p-menthan-4-ol, outperforming both homogeneous iridium and commercial palladium catalysts in activity, selectivity, and stability.

Keywords:

diastereoselective hydrogenation heterogenized complex hybrid catalysts iridium supported catalysts

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Area of Science:

Organometallic Chemistry
Catalysis
Organic Synthesis

Background:

Terpinen-4-ol hydrogenation is crucial for producing cis p-menthan-4-ol.
Developing highly selective and stable catalysts remains a challenge.
Supported catalysts offer potential advantages in activity and recyclability.

Purpose of the Study:

To synthesize and characterize a novel supported Iridium-N-heterocyclic carbene (Ir(NHC)) catalyst.
To evaluate its performance in the selective hydrogenation of terpinen-4-ol.
To compare its efficacy against a homogeneous iridium complex and a commercial palladium on carbon (Pd/C) catalyst.

Main Methods:

Synthesis of a supported Ir(NHC) catalyst.
Hydrogenation reactions of terpinen-4-ol under varying conditions.
Analysis of reaction products using chromatography and spectroscopy.
Comparison of catalyst activity, selectivity, and stability.

Main Results:

The supported Ir catalyst demonstrated superior selectivity (92%) compared to Pd/C (42%) at 80°C.
The solid Ir catalyst exhibited higher activity, selectivity, and stability than its homogeneous iridium counterpart.
This represents the first instance of a supported catalyst outperforming a homogeneous complex in diastereoselective hydrogenation.

Conclusions:

Supported Ir(NHC) catalysts are highly effective for the diastereoselective hydrogenation of terpinen-4-ol.
The supported catalyst offers significant advantages over homogeneous iridium and commercial palladium catalysts.
This work paves the way for more efficient and sustainable catalytic processes in organic synthesis.